How to Save Vacation Days to Take Surprise Trips (or any other vacation)!


This is a topic near and dear to our hearts - for the few of you that don't know, we work full-time jobs and still manage to travel all over the world. In the past year alone, we have taken 13 trips with about half of them being overseas. We aren't telling you this to brag, but just as a starting point to let you know that we know what we're talking about! Not all of you will be able to follow all of our suggestions, but here is an insider's look at how to make it all work:

1. Make Traveling a Priority/Goal

This is the most important tip on here because without making it a priority, all the other tips fall flat. This really isn't really as hard as it seems, it's more just a state of mind than anything you actually have to do.

2. Plan/Book Ahead

Once you have made traveling a priority, take a look at your office holiday calendar, are there any weeks where you have one or more days off? If so, those are your first preference travel weeks/dates. If you happen to have a week or even a pay period with 2 holidays - even better. Just keep in mind, if they are popular holidays (like Christmas) chances are that flight prices will be higher so you'll need to take that into account. The sooner you've identified the best dates for you, the better because you'll have more time to plan your trip or if you are adventurous and are going on a surprise trip, the more options we'll have of where to send you!

3. Flexible Work Days/Teleworking

This is probably the real secret to taking many trips while working. If you are fortunate enough to have flexibility in your workplace, figure out a way to  use it! I (Roshni) work 9 hour days to have every other Friday off and I can move that day off to any day of the pay period, for example, next to a holiday for a 4 day weekend. Jeff doesn't have this option in his office, but is able to telecommute and put in extra hours on some days to work fewer hours on other days. The name of the game is to smash as many non-work days into a short period of time.

4. Understand The Week/Weekend Trade-off

If you have followed the tips above, you should now be able to identify a few weeks out of the year where you'll be able to take a whole 9 days off by only taking 32 vacation hours (4 days at 8 hours of leave each) - and if you have a flexible schedule, you might be able to cut that down even more! Leaving Friday night and coming back a week later on a Sunday maximizes the time you have off. If you can telework or have flexible work days, you can take this to the next level by adding those days onto either end of your vacation and get as many as 10 or 11 full vacation days for the same 32 hours of leave.

5. Find Out Who Has The Least Leave

When traveling with friends or family, there is always one person who has the least amount of leave. For me and Jeff, it's always Jeff - he just gets less leave per year and has less holidays than I do. Because we are aware of this, we value the days he gets off more and prefer to travel over a holiday he has rather than just one that I alone get off.  

Putting it all together, an example:

So all of this is just words until we actually show you what we mean. It's October 2017 and since traveling is always a priority for us (#1), we've taken a look at our holiday calendars for 2018 (#2) and have found that unlike other years, Jeff (who is our vacation hold up #5) actually has 2 days off over the 4th of July in 2018. This is perfect because he would only need to take 24 hours of vacation in order to have a full 9 day trip (#4). Even though I only have 1 day off for the 4th, I am already planning to move my flexible day off to the same day Jeff has off to match his leave (#3). Hope all of this makes sense and feel free to contact us if you have any questions!

If you are ready to get started on your own adventure, fill out our trip survey and we will be sure to maximize your vacation time!